7 Fresh Ways To Wear Dresses With Boots This Fall

fall dresses with boots
Photographed by Daniel Jackson, Vogue, October 2015 

All products featured on Vogue are independently selected by our editors. However, we may receive compensation from retailers and/or from purchases of products through these links.

Pairing a fabulous dress with a great pair of boots is a perennially reliable outfit formula for fall. There’s endless possibilities, depending on your own personal style of course. Slip into a cozy sweater dress or a ruffled prairie midi, and lace up in one of the season’s trendy boots like flat, mid-calf boots or chunky pull-ons. Or opt for a timeless silhouette like a knee high or lace-up combat. No matter the occasion, a dress and boot combo is an easy go-to for any fall activity, from a weekend upstate to a nice outdoor dinner.

Here, 7 chic ways to style fall dresses with boots to get you started.

Practical Prairie

Toughen up a romantic, frilled dress with a pair of lace-up boots. 

Image may contain: Clothing, Dress, Apparel, Sleeve, Robe, Fashion, Human, Person, Evening Dress, and Gown

Free People Rare Feeling pleated maxi dress

Image may contain: Shoe, Clothing, Footwear, Apparel, and Boot

Sam Edelman Garret combat platform boots

Can’t Believe It’s Not Butter

Melt into a turtleneck sweater dress and ultra-soft leather knee highs for maximum coziness. 

Image may contain: Clothing, Apparel, Sweater, Sleeve, Cardigan, and Long Sleeve

Michael Michael Kors ribbed-knit turtleneck minidress

Image may contain: Clothing, Apparel, Footwear, and Boot

By Far Steve 45 leather knee-high boots

Fall Into Winter 

These sweet snow boots will be sure to sell out long before the first frost. Snag them while you can, and pair them with a tiered babydoll. 

Image may contain: Clothing, Apparel, Robe, Fashion, Kimono, and Gown

Merlette Astell floralprint babydoll dress

Image may contain: Clothing, Apparel, Footwear, and Boot

Ganni leather and linen boots

Case In Point

Make a subtly smooth statement in ultra-sharp ankle booties and a sleek pointed-collar shirt dress.

Image may contain: Clothing, Overcoat, Apparel, Coat, Sleeve, Trench Coat, Long Sleeve, and Suit

Staud Cest Zipper Ponte maxi dress

Image may contain: Clothing, Apparel, Shoe, Footwear, High Heel, and Heel

Manu Atelier duck boots

Match the Season

Channel fall in autumnal florals and classic brown leather.

Image may contain: Dress, Clothing, Apparel, and Sleeve

Banjanan Hana floral-print cotton dress

Image may contain: Clothing, Apparel, Footwear, Riding Boot, Boot, Shoe, and Sock

J.Crew tall slouch Willa boots

Twice-as-Nice Knits

You can now literally dress in head-to-toe knits. 

Image may contain: Home Decor, Linen, Clothing, Apparel, and Sleeve

Telfar sweater tank dress

Image may contain: Clothing, Apparel, Footwear, and Boot

Chloé Franne ribbed wool ankle boots

Rain Check

Pairing a pleated fall dress with short, waterproof boots has you ready for any occasion.

Image may contain: Clothing, Apparel, Sleeve, Long Sleeve, and Pajamas

Thebe Magugu knitted dress

Image may contain: Clothing, Apparel, Footwear, Boot, and Riding Boot

Bottega Veneta BV Puddle rain boots